


Sweet Temptations & Stolen Kisses (AKA: My Boyfriend is a Problem)

by TrashTheater



Category: Undertale
Genre: Anxiety, Cash has a huge agoraphilia/exhibitionism kink, Fluff, HorrorTale, M/M, Sugar in Skirts, Sugar may or may not indulge this, Swapfell Purple, Vaginal, body issues, ecto-breasts, followed by unapologetic smut
Language: English
Status: In-Progress
Published: 2020-05-02
Updated: 2020-05-02
Packaged: 2021-03-01 23:01:54
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,589
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23961190
Author URL: https://archiveofourown.org/users/TrashTheater/pseuds/TrashTheater
Summary: A short series of loosely related SweetMoney dates!Date 1: Cash and Sugar go for a drive, but Sugar is a little too cute for Cash to handle.Date 2: [TBA]Date 3: [TBA]
Relationships: Cash/Sugar, Papyrus/Papyrus, SweetMoney
Comments: 3
Kudos: 39





	Sweet Temptations & Stolen Kisses (AKA: My Boyfriend is a Problem)

**Author's Note:**

> Ah, the weather is starting to warm up, and in honor of the nicer weather I’m brushing up the shorts I made back when I thought I could write this ship out of my system (spoilers: I could not. It’s stuck now. It’s a _problem_ now). These can be read as individual one-shots, and do not inherently follow Take it All, although I am personally viewing this as related.

Not that Sugar was concerned or anything, but it was the eight time he’d rushed back to his room to make sure that his outfit was absolutely _perfect_ before Cash got there to pick him up for their date. 

Yes, he thought, beaming at his reflection in the full length mirror. Everything was fine. His outfit was still very cute. Nothing was wrong, and he pointedly shoo’d away those nagging little doubts that kept creeping into his thoughts. 

Even the weather was perfect! Sunny and warm, with puffy white clouds that denied any argument that they weren’t just magically-suspended overstuffed-pillows hanging in the stratosphere. Truly ideal weather for whatever sort of mysterious activity Cash had planned. He’d hadn't told Sugar what, exactly, they would be doing, so picking out the absolutely perfect date-outfit had taken significantly longer than he would have liked. 

But—he thought with a swell of pride—he had quite hit the nail on the proverbial head. 

Sugar twisted back and forth, admiring the way his skirt fluttered in the mirror, his image framed by the sparkly stickers he’d layered up and down the side. It was a bouncy thing, made with layers of silky white material that flared when he moved. It was (perhaps) a little short, Sugar thought as he brushed a hand over the rippling fabric, but he was pretty sure Cash would be the opposite of bothered by that. 

Hanging off his shoulders by two thin straps was the softest shirt he owned. The lavender top felt almost like a sweater, but was thin enough to be cool even in the warm, summer sun, and clung to him flatteringly. The way the wide neck folded over his arms and across his breasts had the effect of making them look larger, Sugar thought delighted, and left his delicate shoulders on display. The thin straps did nothing to hide the lacy black straps of his bra either, the dark material easily drawing the eye. 

Contrasting the short skirt was a pair of tight, black socks that ran all the way up to mid-thigh. They stood out nicely against his white bones, and freshly-cleaned mary janes.

To finish off the look, Sugar had found these adorable little flat-backed rhinestone crystals. It had taken forever to apply the bone-safe glue and carefully arrange them in an organized cluttered just around his sockets, but it had been worth it. They sparkled, catching in the light as he turned his head. 

All in all, he felt remarkably adorable. In fact... he even felt a little sexy~

But...

well...

actually...

...it really wasn't working, was it? 

Twisting a few more times, Sugar's expression faltered. No, the outfit was plenty cute. The issue was him, wasn't it? Nothing sat right on his skinny bones. The short skirt and tight socks only served to accentuate the lankiness of his legs, and his exposed shoulders emphasized how truely dull and brittle his bones were. The shirt didn't really enlarge anything. Only tried (and _failed_ ) to hide how small his breasts were, reflecting his abysmally small magic-pool. Trying to draw attention to them with a cute bra seemed terribly childish to be honest...

And the sparkles were stupid! They were too much! He didn't even know where they were going. They were obscured behind his large-framed glasses and far too flashy without them. 

He **had** to change. 

Racing back to the closet, he yanked back out the items he'd discarded earlier, throwing them on the bed. There had to be time to find an outfit that would cover him better, but he'd never be able to scrub off the rhinestones. Hopefully, Cash wouldn't notice them. Maybe he should wear a hat? Maybe he should wear a bag...

That would be subtle.

Sugar had just started sorting through the mess of options when a familiar, rhythmic-knocking started up from his front door. 

He winced. 

Too little too late...

He tossed one last look in the mirror and tried to summon even a spark of the confidence he'd had a few minutes ago. Nothing came. He wondered why Cash was willing to put up with him at all. 

Steeling himself as best he could Sugar rushed down the stairs, calling out so Cash knew he'd heard. Taking one more calming breath, Sugar hesitantly creaked open the door. 

His soul dropped to his non-existent stomach. 

Cash was standing there with his usual good-natured grin. Wearing his usual black shirt, and his usual black shorts, and his usual heavy jacket, looking just as usual, and normal, and _casual_ , as ever. 

Anxiety scattered like spiders across Sugar's body. It _was_ a date, wasn't it? Had he misunderstood? Oh god, he was going to look ridiculous all dressed up like that! He wanted nothing more than to crawl into the nearest hole and just wither out of existence. 

"hey sweetie," Cash said, looking like totally-not-a-idiot as he stood in the warm sun. Everything about him was relaxed and comfortable, fully prepared for this not-a-date. "ready to go?"

"Um..." Sugar hunched a little farther behind the door. He could say 'no'. Slam the door and run, find something normal to wear, but even if he did there was nothing he could do about his eyes without making Cash wait on him. 

And… he had just been so excited to wear something cute for his boyfriend. 

"Yes…?" he muttered, regretting it instantly. "...I'm… all set."

"great," Cash replied. He didn't say anything or make any sort of motion forward, but the ‘well, you're going to have to come out then’ hung between them as he shifted from one foot to the other. 

Taking a deep breath, Sugar opened the door properly, hoping Cash's response wasn't as bad as he feared. 

It was _so much worse_.

Cash froze completely, even his bad socket going wide as they dropped down, lingering over every inch of him. Sugar felt his skull flush deeply as Cash silently took in every mistake, every bad decision he'd made. Already he could feel tears threatening at the edge of his sockets and Cash hadn't even gotten a word out. 

Sugar slammed the door and locked it, keeping his head down as he rushed past the petrified skeleton towards the car parked in his driveway. "W-Well, w-we better get going then."

Cash was slow to follow, barely mumbling a “yeah...” as Sugar hurried over to the passenger side. He let himself in, the leather of the seats warm against the exposed strip of bone between his skirt and the top of his socks. He was buckled before Cash even reached the door. 

Cash had a nice car. He said he’d won it in a poker game and any other day cruising down those long quiet roads would have been blissful. With the top down, the sun could beat gently down on them, the temperature regulated by the cool breeze as they drove down the atmospherically-delightful back roads of Sugar's neighborhood. Sugar tried to relax and stay in the moment, pretending they were still out on that romantic outing he'd been dreaming about all day. 

But he couldn't. It was impossible. 

Cash was abnormally silent, staring hard out the front window as he drove. His one hand gripped the steering wheel too tightly, while the other curled up against the side of his teeth, his elbow propped on the door. Sugar didn't miss the way his eye would flicker over, running him up and down, lingering on every spot Sugar had hoped he would notice and now just wished he could cover up. It had been so childish to let his imagination run away with him like that and now he was paying for it, cutting himself on the splintered remains of that optimism. 

Cash's attention turned back to the road, and barely a few minutes into the drive, he was suddenly veering down one of the sideroads. Sugar had never been down that road before. There weren't any signs or advertisements for anything in particular but when Cash started scanning the area Sugar joined him, trying to guess where they were going before they got there. 

They swerved—a little too quickly—into a deserted parking lot. Sugar stared up at the small white building as Cash whipped into a parking spot, scrambling to get his seat belt off.

"Is that a church?" Sugar asked, following his example. The seatbelt unlatched with a click, but he didn’t have time to reach for the door handle before Cash was leaning over him, yanking him into a deep kiss. 

Sugar squeaked, caught off guard as Cash invaded his mouth, eager and hungry as usual, effortlessly encouraging Sugar's tongue to form even as he squirmed shyly. 

Cash was breathless when he pulled away. "this isn't where we're going," he said, looking over him with an expression that made Sugar flutter. "i just- _damn_ , baby." 

"You… you like it?" The excitement finally started to bubble up again. 

"like it? sugar-baby, i can't keep my eye off ya-" His hand dropped down, petting over the soft fabric of his shirt as it circled around his waist, pulling him close. "-hands neither." He chuckled, huskily, before kissing him again. 

Sugar felt heat spread across his body as the kisses devolved into a proper make out session, Cash stoking his desire with each frantic caress. Sugar kissed back with vigor, relieved he hadn't made a complete fool of himself, and weak in the face of Cash's desperation. It wasn't long before Cash grabbed his hips and hoisted him up onto his lap. 

Sugar blushed, startled to find himself straddling his boyfriend. Cash just smirked, taking a moment to recline the seat so he could lean back and admire the sight. 

"god, you look so pretty..." he whispered distractedly, almost like he hadn't intended to say it out loud. Sugar squirmed happily, feeling hands slid down his legs before creeping up to tease under his skirt. "...and so unbearably fuckable." 

Sugar pouted, although it did little to hide his obvious pleasure at the attention. Feeling bold, he leaned forward, pressing his body flush against Cash, kissing him again. He could feel the heat of Cash’s magic beneath him and he shyly pushed forward, grinding against him. 

Cash panted against his mouth. His hands climbed up to Sugar’s hips, pulling him closer as he rocked back. Sugar shuddered, pleasant tingles running up his spine. 

Fingers hooked into his panties, eagerly peeling them off and dragging them down to his knees. Sugar pulled back with a blush. “Cash...” he whined, glancing around at the wide open parking lot they were seated it, in full view of the sun and god himself. 

“sugar,” Cash breathed, everything about his expression screaming his love and adoration, and that was all it took. 

It took some finagling, but they got his panties off, tossed carelessly into the backseat as Sugar slipped his hands into black shorts to find that dark purple magic taunting him. Cash groaned into his mouth while Sugar played along the head, grasping the shaft to give a few firm pumps. 

“yer gonna drive me nuts, sweetie,” Cash said, shoving his shorts out of the way, and snatching Sugar’s hips to yank him closer. “can ya lower yerself? please, baby? all pretty like this, just for me. wanna see ya bounce on my cock. gotta see ya. Please?” 

Sugar flushed, fingers spreading over Cash’s chest to support himself. He loved when Cash said those sorts of dirty things. Loved the way he looked, reclined in the seat beneath him, gazing up like Sugar was something beautiful; something awe inspiring…

...Something to be worshiped. 

Reaching down to line him up, Sugar sank down on that heavy cock with a mewl. 

There was only a twinge of discomfort as Sugar was spread open, wet and aroused enough to take the massive girth without too much exertion. His body was starting to become familiar with the size, given how often those innocent little dates had ended up in the bedroom. Or in a back alley... or a public restroom... or that one time in a garage... In retrospect there was a noticeable pattern here, and Sugar would have to think more about that when he wasn’t too busy pulling himself back up and sinking all the way back down over that glorious piece of magic. 

“fuck, sweet-thing,” Cash groaned, struggling not to thrust upward. “look’it you. so gorgeous...” 

The skirt fluttered as Sugar picked up speed, the heat already coiling up inside him. “C-Cash, s-stop it...” 

“naw, precious, can’t.” He grunted at a particularly hard bounce, his hands tightening on Sugar’s hips as he pulled him down, hips bucking up in response. “fuck-! i’m so lucky...!” 

Sugar whined, throwing his head back as he rocked harder. It was so deep. So rough-! So _scandalous-!_ Hitting everything inside him that made him see stars. It built too quickly, toes curling in pleasure as his rhythm faltered. “Cash…! O-Oh Cash-!” It was too much, but his hands fisted in Cash’s shirt, tears in his sockets as he slammed down. “I’m gonna-I’m gonna…!” 

“come on, baby. cum for me…!” 

The coil snapped and he cried out, trembling as orgasm rushed over him. Cash frantically surged up, roughly riding him through the climax, gasping out ‘god!’ and ‘sugar!’ until he stiffened, and warmth spilled inside. 

Sugar collapsed, breathing hard, against his boyfriend's shoulder. The sun continued to layer warmth across his back. Under other circumstances, it would be a lovely place to take a nap. Sugar’s weak constitution meant he was always thoroughly worn out after these wonderful encounters, and he hoped he still had enough energy for wherever Cash had wanted to take him. 

It wasn’t looking too good as he was awoken from a doze by soft kisses to his neck. 

“sorry, sugar. i went and made us late.” Cash chuckled. “i mean, personally i think _you_ went and made us late...” 

Sugar shifted, letting Cash help him up and back into his seat where he collapsed again into the soft, warm leather. “That certainly isn’t what happened, you cod...” 

Cash laughed, a light, satisfied sound as he fixed his clothes, and played with the seat until it was back in position. “guess we’ll have to agree to disagree.” He turned around and backed out of the lot. 

The soft wind was nice when Cash reached the main road again, starting a steady pace along that long, winding road. Sugar just sighed contently, snuggling into the seat. He noticed Cash glancing back over at him, and hoped that he didn’t look too disheveled now, all tired and flushed from their detour. His body was still tingling pleasantly, and would probably do so most of the day. 

But Cash kept glancing over at him as they drove, expression hardening after a few minutes, hands tight on the wheel. Sugar squirmed, feeling embarrassed, and strangely exposed. He reached down to run his hand over the too-short skirt, smoothing it down, before he realized what was bothering him with a shy gasp. 

He twisted around to scour the backseat, coming up empty handed. Clutching his legs together, he turned back to Cash pleadingly. “C-Cash? W-Where are my panties?” 

The other stiffened, spine ramrod, as he shot one more simmering look to the side. Sugar gasped as the car jerked and suddenly they were cutting back down another side road. 

“i’m such a bad boyfriend...” Cash muttered, tone dripping with lust. 

They never did make it to that date. 

**Author's Note:**

> I hope you liked it! I wanted to wait a little later in the summer for these, but I’ve been sitting on this one for so long now and I just wanted to get it up. I have the next two chapters outlined, but I don’t know when I’ll finish them since I’m (trying) to focus on my bigger stories. But all three will be mostly stand alone oneshots, so... 
> 
> Please let me know what you think! I’m always excited to hear from you even if I’m not great at replying!


End file.
